(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine supplier

Name
(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine
EINECS 616-378-0
CAS No. 767340-03-4
Article Data17
CAS DataBase
Density 1.6 g/cm³
Solubility
Melting Point 178-180°C
Formula C₁₆H₁₃F₆N₅O
Boiling Point 555.1 °C at 760 mmHg
Molecular Weight 405.303
Flash Point 289.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,2,4-Triazolo[4,3-a]pyrazine,7-[(2Z)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)-2-butenyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-(9CI);(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine;(2Z)-3-Amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-2-buten-1-one;
PSA 77.04000
LogP 2.77990

Synthetic route

: 764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
With ammonium hydroxide; ammonium acetate In methanol at 58℃; for 0.5h;	92%
With ammonium acetate In methanol at 40 - 45℃; Large scale reaction;	82%
With ammonia In methanol at 25 - 65℃;	79.8%

: 763105-70-0
2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / methanol; water / 0.75 h / 55 °C 2.1: ISOPROPYLAMIDE / 40 - 70 °C 2.2: 20 - 45 °C 3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride / methanol; water / 0.75 h / 55 °C 2.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C 2.2: 3 - 5 h / 20 - 45 °C 3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride / methanol; water / 0.75 h / 55 °C 2.1: ISOPROPYLAMIDE / 70 °C 2.2: 3 - 5 h / 20 - 30 °C 3.1: ammonium acetate; ammonia / methanol; water / 2 h / Heating / reflux View Scheme

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 2 - 3 h / 0 - 40 °C 2.1: ISOPROPYLAMIDE / 40 - 70 °C 2.2: 20 - 45 °C 3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 20 - 40 °C 1.2: 2 - 3 h / 0 - 5 °C 2.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C 2.2: 3 - 5 h / 20 - 45 °C 3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 3 steps 1.1: dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 2 - 3 h / 5 °C 2.1: ISOPROPYLAMIDE / 70 °C 2.2: 3 - 5 h / 20 - 30 °C 3.1: ammonium acetate; ammonia / methanol; water / 2 h / Heating / reflux View Scheme
Multi-step reaction with 3 steps 1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 2: N,N-dimethyl acetamide / 6 h / 70 °C 3: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C 2: N-ethyl-N,N-diisopropylamine / Isopropyl acetate / 5 h / 75 - 80 °C 3: ammonium acetate; ammonium hydroxide / methanol / 0.5 h / 58 °C View Scheme

: 764667-64-3
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ISOPROPYLAMIDE / 40 - 70 °C 1.2: 20 - 45 °C 2.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 2 steps 1.1: ISOPROPYLAMIDE / 70 °C 1.2: 3 - 5 h / 20 - 30 °C 2.1: ammonium acetate; ammonia / methanol; water / 2 h / Heating / reflux View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl acetamide / 6 h / 70 °C 2: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / Isopropyl acetate / 5 h / 75 - 80 °C 2: ammonium acetate; ammonium hydroxide / methanol / 0.5 h / 58 °C View Scheme

: 762240-92-6
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ISOPROPYLAMIDE / 40 - 70 °C 1.2: 20 - 45 °C 2.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C 1.2: 3 - 5 h / 20 - 45 °C 2.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme
Multi-step reaction with 2 steps 1.1: ISOPROPYLAMIDE / 70 °C 1.2: 3 - 5 h / 20 - 30 °C 2.1: ammonium acetate; ammonia / methanol; water / 2 h / Heating / reflux View Scheme

: C15H13F3O4

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C 1.2: 3 - 5 h / 20 - 45 °C 2.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux View Scheme

: 2-oxo-2-(2,4,5-trifluorophenyl)acetamide

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 2: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 3: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 4: N,N-dimethyl acetamide / 6 h / 70 °C 5: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere
2: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C
3: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere
4: N,N-dimethyl acetamide / 6 h / 70 °C
5: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux
View Scheme

: (2,4,5-trifluorophenyl)oxoacetic acid

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 2: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 3: N,N-dimethyl acetamide / 6 h / 70 °C 4: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme

: 86393-34-2
2,4-dichloro-5-fluorobenzoyl chloride

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: potassium fluoride; tetraphenylphosphonium bromide; 18-crown-6 ether / 1,2-dichloro-benzene / 15 h / 120 - 130 °C / Inert atmosphere 2: 1,2-dichloro-benzene / 140 °C 3: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere 4: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 5: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 6: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 7: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 8: N,N-dimethyl acetamide / 6 h / 70 °C 9: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme

Yield

Multi-step reaction with 9 steps
1: potassium fluoride; tetraphenylphosphonium bromide; 18-crown-6 ether / 1,2-dichloro-benzene / 15 h / 120 - 130 °C / Inert atmosphere
2: 1,2-dichloro-benzene / 140 °C
3: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere
4: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere
5: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere
6: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C
7: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere
8: N,N-dimethyl acetamide / 6 h / 70 °C
9: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux
View Scheme

: 2-chloro-4,5-difluorobenzoyl fluoride

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1,2-dichloro-benzene / 140 °C 2: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere 3: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 4: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 5: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 6: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 7: N,N-dimethyl acetamide / 6 h / 70 °C 8: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme

Yield

Multi-step reaction with 8 steps
1: 1,2-dichloro-benzene / 140 °C
2: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere
3: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere
4: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere
5: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C
6: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere
7: N,N-dimethyl acetamide / 6 h / 70 °C
8: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux
View Scheme

: 2,4,5-trifluorobenzoyl fluoride

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere 2: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 3: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 4: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 5: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 6: N,N-dimethyl acetamide / 6 h / 70 °C 7: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere
2: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere
3: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere
4: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C
5: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere
6: N,N-dimethyl acetamide / 6 h / 70 °C
7: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux
View Scheme

: 2,4,5-trifluorobenzene-1-carbonyl cyanide

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 2: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 3: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 4: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 5: N,N-dimethyl acetamide / 6 h / 70 °C 6: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere
2: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere
3: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C
4: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere
5: N,N-dimethyl acetamide / 6 h / 70 °C
6: ammonium acetate; ammonium hydroxide / water; methanol / 2 h / 30 °C / Reflux
View Scheme

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
Stage #1: (Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one With ammonium chloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(di-tert-butylphosphino)ferrocenyl]ethyl-di-2-methylphenylphosphine In methanol at 20℃; for 1h; Stage #2: With hydrogen In methanol at 50℃; under 5171.62 Torr; for 18h; Product distribution / selectivity;	97%
With di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium; hydrogen; (R,S)-t-bu Josiphos In methanol at 20 - 50℃; under 10343.2 Torr; for 14h;	93%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen; ammonium chloride In methanol at 50℃; under 13689.1 Torr; Inert atmosphere; enantioselective reaction;	82%

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: 823817-56-7
(R/S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine

Conditions

Conditions	Yield
With sodium tetrahydroborate; methanesulfonic acid In tetrahydrofuran; isopropyl alcohol at -15 - -5℃; for 4.5h; Reagent/catalyst;	60%
With sodium tetrahydroborate; acetic acid In toluene at 5 - 10℃; for 3h; Product distribution / selectivity;
With sodium tetrahydroborate; formic acid In chlorobenzene at 0 - 5℃; Temperature;

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: 24424-99-5
di-tert-butyl dicarbonate

: 1234321-84-6
(Z)-tert-butyl-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)-but-2-en-2-ylcarbamate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 40h; Reflux;	49.8%

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

A: (S)-Sitagliptin

B: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (S)-Cy2-p-Tol-Biphemp In 2,2,2-trifluoroethanol at 20℃; under 5931.67 Torr; for 20h; Product distribution / selectivity;	A n/a B 94 %Chromat.
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 4,12-bis(diphenylphosphino)-[2.2]-paracyclophane In 2,2,2-trifluoroethanol at 50℃; under 5414.51 Torr; for 18h; Product distribution / selectivity;	A n/a B 58 %Chromat.
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(-)-tetraMe-BITIOP In 2,2,2-trifluoroethanol at 50℃; under 5414.51 Torr; for 18h; Product distribution / selectivity;	A 15 %Chromat. B n/a
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R,R)-1-[1-(di(t-butyl)phosphino)ethyl]-2-(diphenylphosphino)ferrocene In 2,2,2-trifluoroethanol at 20 - 55℃; under 3750.38 Torr; for 26h;

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: sitagliptin phosphate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; formic acid / chlorobenzene / 0 - 5 °C 2.1: ethyl acetate / Reflux 3.1: hydrogenchloride / water 3.2: 0.25 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: (R,S) t-butyl Josiphos; hydrogen / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 13 h / 50 °C / 10343.2 Torr 2: phosphoric acid / water; isopropyl alcohol / 75 °C View Scheme
Multi-step reaction with 3 steps 1.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C 1.2: 13 h / 50 °C / 10343.2 Torr 2.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C 3.1: 1 - 8 h / 58 - 140 °C View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; isopropyl alcohol / 4.5 h / -15 - -5 °C 2: methanol; isopropyl alcohol / 1 h / 65 °C 3: phosphoric acid / isopropyl alcohol / 1 h / 78 °C View Scheme

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: (R)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one (S)-3-(2-amino-2-oxoethyl)-5-methylhexanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; formic acid / chlorobenzene / 0 - 5 °C 2: ethyl acetate / Reflux View Scheme

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: 654671-77-9
sitagliptin phosphate monohydrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C 1.2: 13 h / 50 °C / 10343.2 Torr 2.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C View Scheme

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: sitagliptin tartrate

: C16H15F6N5O*C4H6O6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; isopropyl alcohol / 4.5 h / -15 - -5 °C 2: methanol / 1 h / 65 °C View Scheme

: 767340-03-4
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

: C16H15F6N5O*C20H18O8

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanesulfonic acid / tetrahydrofuran; isopropyl alcohol / 4.5 h / -15 - -5 °C 2: methanol; isopropyl alcohol / 1 h / 65 °C View Scheme

(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine Specification

The CAS register number of (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine is 767340-03-4. It also can be called as 2-Buten-1-one,3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-,(2Z)- and the systematic name about this chemical is (Z)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one. The molecular formula about this chemical is C₁₆H₁₃F₆N₅O and the molecular weight is 405.30. It belongs to the following product categories, such as All Inhibitors; Heterocycles; Inhibitors; Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals; Pyrazine and so on.

Physical properties about (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine are: (1)ACD/LogP: 1.29; (2)ACD/LogD (pH 5.5): 1.27; (3)ACD/LogD (pH 7.4): 1.29; (4)#H bond acceptors: 6; (5)#H bond donors: 2; (6)#Freely Rotating Bonds: 4; (7)Polar Surface Area: 77.04Å²; (8)Index of Refraction: 1.59; (9)Molar Refractivity: 85.17 cm³; (10)Molar Volume: 252.3 cm³; (11)Polarizability: 33.76x10^-24cm³; (12)Surface Tension: 42.4 dyne/cm; (13)Enthalpy of Vaporization: 83.63 kJ/mol; (14)Boiling Point: 555.1 °C at 760 mmHg; (15)Vapour Pressure: 2.32E-12 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: c1c(c(cc(c1F)F)F)CC(=CC(=O)N2CCn3c(nnc3C(F)(F)F)C2)N
(2)InChI: InChI=1/C16H13F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4-6H,1-3,7,23H2/b9-5-
(3)InChIKey: RLSFDUAUKXKPCZ-UITAMQMPBR
(4)Std. InChI: InChI=1S/C16H13F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4-6H,1-3,7,23H2/b9-5-
(5)Std. InChIKey: RLSFDUAUKXKPCZ-UITAMQMPSA-N

Product Name

(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine

Synthetic route

(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine Specification

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